TWI294905B - Novel polymers for use in optical devices - Google Patents
Novel polymers for use in optical devices Download PDFInfo
- Publication number
- TWI294905B TWI294905B TW092130088A TW92130088A TWI294905B TW I294905 B TWI294905 B TW I294905B TW 092130088 A TW092130088 A TW 092130088A TW 92130088 A TW92130088 A TW 92130088A TW I294905 B TWI294905 B TW I294905B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- alkyl
- aryl
- substituted
- crc18
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 116
- 230000003287 optical effect Effects 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 257
- -1 p-hydroxyphenyl Chemical group 0.000 claims description 157
- 125000003118 aryl group Chemical group 0.000 claims description 122
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 89
- 239000004305 biphenyl Substances 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 235000010290 biphenyl Nutrition 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 239000000126 substance Substances 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 239000000178 monomer Substances 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 35
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 8
- LXXQADRIIXEBHT-UHFFFAOYSA-N 2,4,6-tris(4-bromophenyl)pyrimidine Chemical compound C1=CC(Br)=CC=C1C1=CC(C=2C=CC(Br)=CC=2)=NC(C=2C=CC(Br)=CC=2)=N1 LXXQADRIIXEBHT-UHFFFAOYSA-N 0.000 claims 5
- AXNLMCWMZXDBNC-UHFFFAOYSA-N 4,6-bis(4-bromophenyl)-2-phenylpyrimidine Chemical compound C1=CC(Br)=CC=C1C1=CC(C=2C=CC(Br)=CC=2)=NC(C=2C=CC=CC=2)=N1 AXNLMCWMZXDBNC-UHFFFAOYSA-N 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- PFLPZHPQFNFTRF-UHFFFAOYSA-N 2-(4-bromophenyl)pyrimidine Chemical compound C1=CC(Br)=CC=C1C1=NC=CC=N1 PFLPZHPQFNFTRF-UHFFFAOYSA-N 0.000 claims 1
- 101100379727 Caenorhabditis elegans arl-5 gene Proteins 0.000 claims 1
- 241000555745 Sciuridae Species 0.000 claims 1
- 229910052747 lanthanoid Inorganic materials 0.000 claims 1
- 150000002602 lanthanoids Chemical class 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 102220243367 rs1193754562 Human genes 0.000 claims 1
- 239000002585 base Substances 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000010410 layer Substances 0.000 description 46
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 37
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 238000000034 method Methods 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000011651 chromium Substances 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
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- 239000002244 precipitate Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
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- 150000001875 compounds Chemical class 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 229910052738 indium Inorganic materials 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 description 6
- ZENOGNCMCJNJAJ-UHFFFAOYSA-N CCCCCCC1=CC=C(C=C1)C2=CC=CC=C2C3=CC=C(C=C3)Br Chemical group CCCCCCC1=CC=C(C=C1)C2=CC=CC=C2C3=CC=C(C=C3)Br ZENOGNCMCJNJAJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- YXLVUDFNUJSHCJ-UHFFFAOYSA-N 2-[2-(4-bromophenyl)phenyl]naphthalene Chemical group BrC1=CC=C(C=C1)C1=CC=CC=C1C1=CC=C2C=CC=CC2=C1 YXLVUDFNUJSHCJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HOQVGPXSUIHTPD-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1C(C=CC=C1)=C1C(C=C1)=CC=C1Br Chemical group CC(C)(C)C(C=C1)=CC=C1C(C=CC=C1)=C1C(C=C1)=CC=C1Br HOQVGPXSUIHTPD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910000861 Mg alloy Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002114 valyl group Chemical group 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0633—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0225244A GB0225244D0 (en) | 2002-10-30 | 2002-10-30 | Electroluminescent device |
| EP03101113 | 2003-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200422377A TW200422377A (en) | 2004-11-01 |
| TWI294905B true TWI294905B (en) | 2008-03-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092130088A TWI294905B (en) | 2002-10-30 | 2003-10-29 | Novel polymers for use in optical devices |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7649077B2 (pt) |
| EP (1) | EP1556435A1 (pt) |
| JP (1) | JP4619944B2 (pt) |
| KR (2) | KR101015045B1 (pt) |
| AU (1) | AU2003283284A1 (pt) |
| BR (1) | BR0315854A (pt) |
| CA (1) | CA2501692A1 (pt) |
| MX (1) | MXPA05004423A (pt) |
| TW (1) | TWI294905B (pt) |
| WO (1) | WO2004039864A1 (pt) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG111090A1 (en) * | 2002-10-25 | 2005-05-30 | Agency Science Tech & Res | Cationic water-soluble conjugated polymers and their precursors |
| US8492749B2 (en) | 2004-12-23 | 2013-07-23 | Basf Se | Electroluminescent metal complexes with nucleophilic carbene ligands |
| TW200716536A (en) * | 2005-06-09 | 2007-05-01 | Chugai Pharmaceutical Co Ltd | Vitamin D compounds |
| JP5446096B2 (ja) * | 2007-02-06 | 2014-03-19 | 住友化学株式会社 | 組成物及び該組成物を用いてなる発光素子 |
| US7926697B2 (en) * | 2007-09-19 | 2011-04-19 | Intel Corporation | Underfill formulation and method of increasing an adhesion property of same |
| TW201008973A (en) * | 2008-04-24 | 2010-03-01 | Showa Denko Kk | Charge-transporting polymer compound and organic electroluminescent device using the same |
| JP5544775B2 (ja) | 2008-07-29 | 2014-07-09 | 住友化学株式会社 | 燐光発光性化合物を含む組成物及び該組成物を用いてなる発光素子 |
| JP5672681B2 (ja) * | 2008-09-18 | 2015-02-18 | 三菱化学株式会社 | 電荷輸送膜用組成物、有機電界発光素子、有機ｅｌディスプレイ及び有機ｅｌ照明 |
| JP5515542B2 (ja) * | 2008-10-06 | 2014-06-11 | 住友化学株式会社 | 含窒素複素環構造を含む高分子化合物 |
| TWI482758B (zh) | 2009-08-21 | 2015-05-01 | Tosoh Corp | 環狀氮雜衍生物及其製造方法和以該環狀氮雜苯衍生物為構成成分之有機電致發光元件 |
| EP2647655A4 (en) * | 2010-11-30 | 2017-08-09 | Sumitomo Chemical Company Limited | High molecular compound, method for producing same, and light-emitting element |
| TWI613195B (zh) | 2011-08-25 | 2018-02-01 | 半導體能源研究所股份有限公司 | 發光元件，發光裝置，電子裝置，照明裝置以及新穎有機化合物 |
| EP2778160B1 (en) | 2011-11-11 | 2018-01-10 | Tosoh Corporation | Cyclic azine compound having nitrogen-containing fused aromatic group, method for producing same, and organic electroluminescent element using same as constituent component |
| US9059411B2 (en) | 2012-02-29 | 2015-06-16 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| KR101335161B1 (ko) * | 2012-06-18 | 2013-11-29 | (주)원우시스템즈 | 개량된 태양전지 품질 측정 방법 및 장치 |
| JP6312960B2 (ja) | 2012-08-03 | 2018-04-18 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、照明装置及び複素環化合物 |
| US9444059B2 (en) | 2013-02-21 | 2016-09-13 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
| KR102457008B1 (ko) | 2014-05-23 | 2022-10-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 헤테로고리 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
| JP6684085B2 (ja) | 2014-12-19 | 2020-04-22 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
| KR20170117084A (ko) | 2015-02-18 | 2017-10-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 표시 모듈, 조명 모듈, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치 |
| KR20210018105A (ko) | 2019-08-09 | 2021-02-17 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 디바이스, 발광 장치, 전자 기기, 및 조명 장치 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0069058B1 (de) * | 1981-06-10 | 1986-02-26 | Ciba-Geigy Ag | 2-Substituierte 5-Vinylpyrimidine, daraus herstellbare Polymere und Verfahren zu deren Herstellung |
| JP3760491B2 (ja) * | 1995-10-16 | 2006-03-29 | 住友化学株式会社 | 高分子蛍光体、その製造方法及び有機エレクトロルミネッセンス素子 |
| JP3546645B2 (ja) * | 1996-08-21 | 2004-07-28 | 住友化学工業株式会社 | 高分子蛍光体および有機エレクトロルミネッセンス素子 |
| KR100521299B1 (ko) | 1996-09-16 | 2005-10-14 | 코비온 오르가닉 세미컨덕터즈 게엠베하 | 트리아진 중합체, 이의 사용 방법, 및 이를 함유하는 전자발광 장치 |
| KR0176336B1 (ko) * | 1996-12-31 | 1999-04-01 | 박원훈 | 아세틸렌기를 함유한 플로렌계 교대 공중합체 및 이를 이용한 전계발광소자 |
| JPH10324870A (ja) * | 1997-05-23 | 1998-12-08 | Sumitomo Chem Co Ltd | 高分子蛍光体および有機エレクトロルミネッセンス素子 |
| JP4934888B2 (ja) * | 1999-04-09 | 2012-05-23 | 住友化学株式会社 | 高分子蛍光体およびそれを用いた高分子発光素子 |
| TW484341B (en) * | 1999-08-03 | 2002-04-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light emitting device |
| JP2001226469A (ja) | 1999-12-10 | 2001-08-21 | Fuji Photo Film Co Ltd | 新規重合体、発光素子材料およびそれを使用した発光素子 |
| US20010012572A1 (en) * | 1999-12-10 | 2001-08-09 | Katsumi Araki | Novel polymer, light-emitting device material and light-emitting device using the same |
| TW572991B (en) * | 1999-12-20 | 2004-01-21 | Sumitomo Chemical Co | High molecular weight fluorescent element, its process, and high molecular weight fluorescent light emission element |
| JP4940493B2 (ja) * | 1999-12-20 | 2012-05-30 | 住友化学株式会社 | 高分子蛍光体、その製造方法および高分子発光素子 |
| TWI238183B (en) * | 2000-01-12 | 2005-08-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emitting device |
| JP2001302793A (ja) * | 2000-02-17 | 2001-10-31 | Fuji Photo Film Co Ltd | 新規重合体、発光素子材料およびそれを使用した発光素子 |
| JP2002105444A (ja) * | 2000-09-29 | 2002-04-10 | Fuji Photo Film Co Ltd | ヘテロ芳香族環含有ビニルモノマーの合成方法、並びにそのモノマーを用いた有機発光素子材料及び有機発光素子 |
| DE10143353A1 (de) * | 2001-09-04 | 2003-03-20 | Covion Organic Semiconductors | Konjugierte Polymere enthaltend Spirobifluoren-Einheiten und deren Verwendung |
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- 2003-10-21 KR KR1020107020815A patent/KR101015045B1/ko not_active IP Right Cessation
- 2003-10-21 WO PCT/EP2003/011634 patent/WO2004039864A1/en active Application Filing
- 2003-10-21 BR BR0315854-3A patent/BR0315854A/pt not_active Application Discontinuation
- 2003-10-21 AU AU2003283284A patent/AU2003283284A1/en not_active Abandoned
- 2003-10-21 EP EP03775209A patent/EP1556435A1/en not_active Withdrawn
- 2003-10-21 CA CA002501692A patent/CA2501692A1/en not_active Abandoned
- 2003-10-21 KR KR1020057007698A patent/KR101015032B1/ko not_active IP Right Cessation
- 2003-10-21 US US10/531,779 patent/US7649077B2/en not_active Expired - Fee Related
- 2003-10-21 JP JP2005501807A patent/JP4619944B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| KR101015045B1 (ko) | 2011-02-16 |
| JP2006504862A (ja) | 2006-02-09 |
| WO2004039864A8 (en) | 2004-08-19 |
| EP1556435A1 (en) | 2005-07-27 |
| WO2004039864A1 (en) | 2004-05-13 |
| CA2501692A1 (en) | 2004-05-13 |
| US7649077B2 (en) | 2010-01-19 |
| KR101015032B1 (ko) | 2011-02-16 |
| TW200422377A (en) | 2004-11-01 |
| US20060025564A1 (en) | 2006-02-02 |
| AU2003283284A1 (en) | 2004-05-25 |
| BR0315854A (pt) | 2005-09-20 |
| MXPA05004423A (es) | 2005-07-26 |
| KR20100119798A (ko) | 2010-11-10 |
| KR20050084618A (ko) | 2005-08-26 |
| JP4619944B2 (ja) | 2011-01-26 |
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